Neither of us said a word, for every time I tried to speak she would place her finger over my lips. We relaxed in this position for several minutes, but when she felt my cock getting hard again, she started moving slowly, just rolling her ass on me, until she gasped sharply and shuddered to a stop.
Then, less than twenty minutes after she’d arrived, she kissed me gratefully, buttoned her blouse, handed me her panties for a keepsake, and left. The next morning one of the office girls told me that Lauren had given birth to a baby girl during the night.
That was the only time I had any physical contact with Lauren, and after she returned to work neither of us ever mentioned the incident. But since that night I get an extraordinary feeling when I see a woman who is expecting, and I certainly understand why those X-rated videos of pregnant ladies are so popular.
—L.C., Flint, Michigan
HE FINDS IT’S NEVER TOO LATE TO LEARN NEW
THINGS—LIKE BEING A WOMAN
At fifty-five years of age, divorced and very active sexually, I had done it all—been there, done that, and got the T-shirt to prove it. As I got older I found that my sexual desire needed to be stimulated by new things, but considering all I had done, I wasn’t sure what it would take to get my hormones running on high again. So I decided to explore new areas of sex play.
Browsing in an adult magazine store one day, I came upon a bunch of fetish magazines—the kind with features such as, “How I Discovered Feet,” or “Six Ways to Whip Your Lover and Make Her Love It!” As I looked through the magazines I came across one devoted to cross-dressing that caught my full attention. There were a lot of pictures, and some of the men dressed like women looked pretty damn good. I bought the magazine and headed for home.
Later that night I read the thing from cover to cover, and found myself getting excited by the stories of these guys who transformed themselves from straight men to gorgeous-looking females, high heels and all. I went to sleep thinking about this, and in the morning I knew I was going to give it a try—even though the thought of a fifty-five-year-old, one-hundred-ninety-pound guy dressed up in drag seemed pretty damn silly.
I used the Internet to search out stories and information on this particular fetish. Much to my surprise, the Web was full of information. I even found businesses that sold the type of items that catered to cross-dressers, from fake tits to strap-on pussies—amazing stuff. With my new knowledge and a pocket full of money, off I went to get myself “dressed up.”
Before the week was out I had purchased stockings, garter belts, high-heeled shoes, and a fancy camisole top, among other things. Naturally, due to my inexperience, I made some poor choices, and some things had to be returned, but I finally was able to settle on an outfit that was very pretty and fit well. Some of my experiences while shopping, the reactions of the clerks and the conversations we had, would make for some interesting stories, but I don’t want to digress. I was finally ready to try out my new look.
Of course you understand that it’s not much fun dressing up in this stuff if you don’t show it to someone and use your new look to get off sexually. I had already made the decision to do that. In for a dollar, in for a dime, or whatever. Although I am generally more attracted to women, I knew that in this outfit I would be most likely to attract men—men looking to get blown by, or to fuck, a cross-dresser. And I decided I was okay with that.
I figured I would start by hitting the local adult shop, and Friday night was the fatal time. When I got home from work I got my stuff together and began my transformation. An hour later it was complete, and there I was, a lovely, but somewhat big, older lady in trashy stockings and heels. The only discrepancy was my cock, which was hard as a rock—a major giveaway for sure!
I put on my overcoat, got in my car and off I went. As I was driving a thought crossed my mind: if I was stopped by a cop and made to get out of the car, I was finished. My ass would be in the station house, with the local papers having a blast reporting on the old guy all dolled up in panties and stockings! I drove very carefully till I got to my destination.
The store was your typical sex joint, with the usual books and magazines, a glory-hole room, a crummy porn theater, and endless rows of videotapes. It was not too busy when I got there, which was a mixed blessing. I wanted to be seen, and at the same time did not want to be seen. But I was there to explore, and I was going through with it. I went up to the counter girl and paid my five bucks to gain entrance into the glory-hole room. The girl looked me over and smiled; she knew what I was doing, and would probably pass the word to the next few customers that I was available.
There were six dark booths with videos playing in them, only one of which was in use. A guy jerking off, was my guess. I placed myself near one of the booths and leaned against the wall, my coat open, my cock hard as nails. What a sight I must have been—high heels, white stockings on my legs, a silky top showing under my coat, and my dick sticking out, waiting for action.
My waiting soon came to an end. The entrance door opened and in came a middle-aged guy about fifty or so, all dressed up in a suit. A married man, I thought, looking to get his dick sucked or maybe suck some himself. Since l was the only person standing in the long narrow hallway, he walked over and leaned against the wall next to me. We were shoulder to shoulder. Then my new friend zipped down his fly and took his cock out, an average cock, uncut and starting to get hard. When I didn’t move, he reached over, took hold of my hand, and placed it on his dick.
Well, I thought, I started this, so I might as well play the game. I began to stroke him a little. His cock was wet with precome. My own dick was throbbing, but he offered no help. I figured my cock would have to wait. But that was all right; I was getting into this now. “Lick your fingers, honey,” the guy whispered, and I did as I was told. Maybe this cross-dressing thing makes you a little submissive? I didn’t know, but I enjoyed feeling that way.
After I stroked him some more he said we needed a bit more privacy, so I moved into the booth and he followed. Inside, with the door closed, he put both hands on my shoulders and pushed me down. I knew what he wanted, and in my new and exciting submissiveness I went down on my knees, my ten-dollar stockings getting fucked up on the come-covered floor. Before my knees hit the floor my mouth was open, like some sort of automatic machine. The guy stuck his uncut cock in my mouth and began to fuck my face. I could feel his hands on my head as he guided his dick into my throat. It was not unpleasant; in fact, it was damned arousing, and I closed my lips around him and did the best I could to make it good. “Yeah, take my come, baby!” he growled. Not a very elegant way to talk to a lady, but it made me suck him harder.
Although it seemed longer, it was really only seconds before the guy shot his load down my throat. I swallowed as much as I could, but swallowing come was new to me, and some of it ran out and down my chin. As soon as the guy finished coming he pulled away, put his cock in his pants, and left.
Slowly I got up, got myself together as best I could, and went out. The girl at the counter knew what I had done, all right—probably the guy leaving had given her a clue. As I went past her she trilled, “Did you have fun, sweetie? Come again sometime.”
Well, I thought, I just might. Even though I hadn’t gotten off, my dick was still hard, and had been for quite a while—not bad for a fifty-five-year-old pervert. I figured I had discovered something just as good as Viagra, and a lot more fun!
—C.P., St. Louis, Missouri
HEARING ABOUT THE MALE PROSTATE, HIS WIFE HAD
TO EXPLORE FOR HERSELF
This is an unabashed thank-you to your publication. Your article about stimulating the prostate has led my wife Josie and me to experience enormous pleasure. I am newly married to the ideal woman, a living, breathing doll straight from your glossy pages.
When I somewhat timidly told my bride about the prostate article, she immediately sat upright in bed, her pink nipples already stiff with excitement.
“Could we do that?” she asked as
I held her in my arms.
“Oh, you little slut.” I laughed. “Yes indeed, if you want to.”
She quickly disappeared under the covers. I felt her breath on my balls, the wetness of her tiny tongue, then the incredible sensation of her gently sucking each testicle into her hot mouth. I couldn’t stand not being able to watch her. I tossed back the covers to find her wild eyes staring up at me adoringly over the head of my stiff penis. She kissed the cheeks of my ass, causing my cock to emit precome, which was soon flowing down my shaft. She looked at me worshipfully, and I gasped as her tongue darted out to lick at my shaft, savoring each drop before reaching the crown. I felt that tongue digging at the tip of my cock as her lips engulfed the head. She took more and more, and finally all of my cock into her sweet, tight mouth, then slowly pulled off. As she released her prize a clear thread of fluid stretched from my cock to her tongue.
Her slender body swung gracefully astride my chest, facing away from me, her smooth bare pussy inches away from my face as she rolled her swollen pink clitoris between her slender fingers. Then she dipped a finger into her dripping cunt for lubrication, and, bending forward, moved that glistening digit between my legs, searching for the entrance to my ass. I held my breath.
“Ready, baby?” I was more than ready, but I gave a gasp as that finger penetrated my anus. As if by instinct it slid all the way in until it found the spot it was seeking. “Is that it, baby?” she asked.
I moaned in response as her finger gently pressed against my sensitive prostate. I had never been harder, and when her mouth returned to my cock she took me straight in to the soft tightness of her throat. The delicious pressure inside my ass was causing the precome to flow as if I was coming, and the sensation was nearly the same. I tangled my fingers tightly in her hair and lost myself in pleasure as she took me even farther into her mouth. I could feel the back of her throat and its tight contractions as she swallowed, trying to gulp down my cock as it fucked her lovely throat.
I thought she would finish me this way, but my ingenious lover had more devilish ideas. I felt her finger slip away as she raised her head from my cock. Straightening up and hitching herself forward, she guided my dripping dick deep inside her womb. Then, with a feline grace, she leaned forward again, reached beneath my swollen balls, and once more found the sweet spot inside my rectum. “Fuck my pussy, baby,” she moaned. “Fuck my pussy while I fuck your ass!”
Fighting my urge for release, I distracted myself by firmly squeezing the cheeks of her perfect bottom. Then, wanting her to receive as well as give, I penetrated her trembling ass with my finger. I could feel my cock through the walls of her pussy. Bending my finger slightly, I could rub the head of my cock through the intervening membrane with every thrust, massaging my cock and her pussy at the same time. Josie’s finger was busy too, stroking my prostate rhythmically. We were both moaning with passion. Finally I roared, “Now!” and we both tumbled heading into ecstasy.
Our honeymoon will never be over.
—C.F., Phoenix, Arizona
HOW TO PLEASURE ANOTHER MAN’S WIFE
AND STILL BE A FAITHFUL HUBBY
My wife Jean and two of her girlfriends went to a house party sponsored by a company that promotes and sells ladies’ personal products. She came home with several sexy items of clothing, along with a pair of vibrating balls meant to be inserted in the vagina, and equipped with a remote-control switch.
Jean is an attractive twenty-six-year-old blonde with a 36-23-36 figure, so when she modeled the lingerie for me I applauded and showed her the woody she had given me. When I asked her about the vibrating balls, she said that they were a free gift from the company and meant to be a joke. But when I persisted, she opened the package for me to examine. When I asked if she’d like to try them, she just shrugged.
Later, when I was going down on her, I deftly opened her wet pussy with one hand and inserted the balls with the other, taking special care to make certain they were positioned firmly against her G-spot. Jean pretended to be oblivious to what I was doing, until I moved up and kissed her with my pussy-soaked lips as I activated the remote.
She smiled and began to say something, but then her eyes closed and her mouth opened, and she began moaning softly with pleasure. When I turned the power higher, she opened her legs, planted her feet close to her ass, and began a slow fucking motion. Her hips moved more vigorously as I moved the power switch to high, and she pulled my face to hers for another kiss, sucking and nibbling at my lips and tongue. She soon had a violent and noisy orgasm, after which she sucked me off with grateful abandon.
The vibrating balls now became a periodic part of our lovemaking, especially when we had anal sex or when Jean was sucking my cock, though I was always a little bit worried that she might inadvertently bite it off.
One night Jean and I were planning to go out with her two friends and their husbands for dinner and dancing. While we were dressing, I noticed the little balls in Jean’s dresser drawer, and suggested that she insert them during our evening out. She thought about it for a minute, then said that she would if the other girls did. She promptly called them, and apparently convinced them that it might be amusing. When I took possession of the remote control, she said, “Be careful with that thing!”
The other girls, as it turned out, hadn’t told their husbands of the secret insertions. During the evening they smiled more than usual, and drank more than usual too. But the secret came out when I displayed my remote. At that point Katie and Tess giggled and pulled out their own remotes from their evening bags. Before either of the husbands could get them, I grabbed the other two remotes, shuffled them along with mine until I no longer knew which was whose, then handed one to each of the other guys. No one in our party objected to my impetuous maneuver. The guys looked amused, and the girls giggled nervously.
Later, while I was slow-dancing with Tess, she suddenly gasped, and her knees buckled. I hung on to her until she recovered, then looked over to see Katie’s husband watching with a grin on his face, delighted that his remote was working on Tess. We decided to finish the dance, but she was soon dry-humping me right on the dance floor in front of everyone, including her husband.
I looked over at Jean, who was taking a sip from her wineglass when she suddenly and unexpectedly set it down and closed her eyes. So Tess’s husband had her remote, which meant that the one I now had was for Katie’s vibrator. I waited until Katie was headed for the ladies’ room, then turned it to high. Katie shrieked and tried to make it back to our table in the midst of the climax she was having in front of a crowd of friends.
Now we always take the equipment with us when we go out with our friends, for we have discovered an acceptable way to pleasure another man’s wife and still remain faithful and devoted husbands.
—F.N., Omaha, Nebraska
SHE HAD NEVER ACTED ON HER CURIOSITY ABOUT
OTHER WOMEN, UNTIL HER COWORKER
WROTE HER A SEXY LETTER
I had known for a while that I wanted to have sex with another woman. My boyfriend Sam (who is now my husband) was of course in love with the idea. To his credit, though, he did not push it at all. We would always comment on the sexy women we saw on the street, and it always made me moist when other females would look at me, but I didn’t have any idea of how to make this fantasy come true. Every month when I got my copy of Penthouse Letters, I would flip right to the “Girl Meets Girl” section and read the most wonderful stories, masturbating over them for hours.
Then I met Sylvia. She walked into my office one day, preparing to start her new job, but that’s not all she started. She stood tall, five feet ten inches, with long red hair and soft pale skin covered with freckles. Her green eyes seemed to stare deep into me, and it gave me a strange feeling. Although I was very attracted to her, I was also kind of nervous. For a few weeks nothing happened at all, and I didn’t really think it would. I just looked at her as another beautiful woman that I could fantasize about. Which I did, all the time. I would
picture her sweet face buried in my pussy, sucking on my clit with that long red hair tickling my thighs, and that was all it would take to make me come all over my fingers.
Then one day at work, Sylvia passed me a letter, and as I read it I realized that she was hitting on me. The letter said that she didn’t want to freak me out, but she had been having sexual dreams about me. My pussy tingled with excitement. I just sat there, not knowing what to do. Finally I got up my nerve and walked over to her desk. I leaned over her, so that my cleavage was right in front of her eyes, and wrote my phone number down, telling her that I thought she needed to call me.
And that night she did. We made small talk for a while, rather awkwardly, and then Sylvia asked me what I thought about her letter. I took a deep breath and told her that I was nervous about it; that I really wanted to have sex with her, but I was still a virgin as far as other women were concerned. Sylvia said she understood, and we decided to “take things slow.”
Over the next few weeks we wrote very explicit notes to each other. The letters got juicier as time passed, and soon I was bringing hers home and jerking off to them, coming almost instantly. One Friday, after I passed Sylvia an especially vivid and nasty letter, I saw her get out of her chair and walk to the bathroom. About ten minutes later, she came back. Passing my desk, she looked around to make sure the coast was clear, then leaned down and stuck two fingers in my mouth. I had never tasted another woman’s come, but I knew that was exactly what I was tasting now. She had gotten so excited reading my story that she’d had to go finger her pussy.
Letters to Penthouse XXVII Page 19
